Azo dye.



UNITED STATES PATENT OFFICE.

mm HBRZBERG. OF OPLAIJEN. NEAR COLOGNE. GERMANY. ASSIGNOB T SYNTHETIC PATENTS (30., INC.. 01' NEW YORK H. Y.. A CORPORATION OF Patented Nov. 16. 1915.

Serial No. 3269.

NEW YORK.

AZO DYE.

1 160 406. Specification of Letters latent in Drawing. Application filed January 20. 1915.

To all whom it may concern:

Be it known that. I. Mam Hnuzumzo, iloctor of philosophy, chemist. citizen of the Barman Empire, residing at Opladen, near Cologne, Germany. have invented new and flll Improvements in Azo Dye. of which i=- following is a specification.

i. I have found that new and valuable disazo ilyestufls can be obtained by coupling the razo compound of a para-diamin of the 'phenyl series. e. g. dianisidm. benzidm. 'din. diaminodiphenylamin. or its sulnic acids. etc, in any course of succesion F! theone hand with a 2.5.7-aminonaphthol 1 ouic acid com d, such as 2.5.7- A 'nonaphthol sulfonic acid. 'Z- henylor fihylamino-inaphthol-T-sulfonic acid, '2- hininoc'o-naphthol-L'F-disulfonic acid, such hompounds having in general the nucleus Qnd on the other hand with such an amino igibstituted derivative of this acid as coniu the substituent in free amino group. is such components e. g. the following are finitahle for being used: metaor paraiminophenyl 2.5.7 aminonapht-hol sulfonic metaor para-aminobenzoyl-liiminonaphthol sulfonic acid. metaor paraflninopheuyl naphthothiazole oxy F511]- 1.;- ic ac para-aminophenyl-naphthimidah xy-T-sulfonic acid. etc- 1 The new matters are after being and pulverized in the shape of their ilkali metal salts generally dark powders fialuble in water with a red to violet to blue gplorstion. They yield upon reduction with gnc powder and acetic acid a aradiamin. g 2.6-diamino-5-naphthol-T-sulfonic acid fipound and a diamino substituted deriva- V of a iiiaminouaptlliltboldsulfonic 2i pound containing in l e si e chain a fin 0 group. They dye cotton from red to a ct to blue shades which are rendered fast washing by an after treatment with foraldehyde.

otrglerfto illustrate the nlew process more P y e ollowing exampe is given. the being by weight .2 parts of anisidin are the tetrazo comgfound is rendered alkaline and is then added to an alkaline solution of 17.8 parts of meta aminophen vlnaphtimidazolc -5 ox v -T- sulfonic acid. The intermediate product separates. It is then added to an alkaline solution of 12 parts of '2-amino-5-naphthol- T-sulfonic acid. After stirring the mixture for one hour. the liquid is heated to C., salted out. filtered off and dried. The color ing matter dyes cotton blue. It is after being dried and pulverized in the shape of its sodium salt a dark blue powder soluble in water with a blue coloration, having in a free state most probably the formula:

I AY and yielding upon reduction with zinc p0wdcr zmd acetic acid dianisidin. lfi-diamino- -naphthol-T-sulfouic acid. meta-aminophenylnaphthimidazole 5 -oxy-6 amino- 7- sulfonic acid.

I claim 1- The herein described new disazo dyestufi's being obtainable from a para-diamin of the diphenjl sericsa 2.5.T-aminonaphth0l sulfonic acid compound and such an amino substituted derivative of this acid as contains in the substituent a free amino group, which dyes are after being dried and pol verized in the shape of their alkali metal salts generally dark powders soluble in water with a red to violet to blue coloration: yielding upon reduction with zinc powder and acetic acid a para-diamiu. a 2.6-diamino- 5-naphthol-T-sulfonic acid compound and a diamino substituted derivative of 2.5.? aminonaphthol sulfouic acid compound containing in the Side chain a free amino group; dveing cotton from red to violetto blue shades which are rendered fast to washing bv an after treatment with formic aldehyde. substantially as described.

'2. The herein described new disazo dyestufl's being obtainable from a para-diamin of the diox diphenrl series a 2.5.7-amin0- naphthol sulfonic acid compound and such an amino substituted derivative of this acid,

as contains in the substituent a free amino group. which dves are after being dried and pulverized in the shape of their alkali metal salts generally dark powders soluble in water with a red to violet to blue coloration; yielding upon reduction with zinc powder and acetic acid a dioIv-para-diamin, a 2.6- diamino-5-naphthol-7-sulfonic acid compound and a diamino substituted derivative of 2.5I-aminonaphthol sulfonic acid compound containing in the side chain a free amino group: dveing cotton from red to violet to blue shades which are rendered fastto washin bv an after treatment with formic aldehvde. substantially as desrribed.

3- The herein described new disazo d ve stuffs being obtainable from a paradlamin of the diphenvl series, a 2.5.7-aminonaphtho] sulfonic acid compound in genera] the following nucleus i 5 I n u I and such an anrituted derivative of this acid ascontaius in thesubstittient a free amino group. which dyes are after being dried and pulverized in the shape of their alkali metal $llt5 enerally dark powders soluble in water with a red to violet to blue coloration: Yielding upon reduction with zinc powder and acetic "acid a Dara-diamin. a 2.6-diamino-5-haphtliolfisulfonic acid compound having in general the following pnl 'i erized in the metal salts generallji dark powders soluble iii (in and such an amino substituted derivative of this acid as contains in the side chain an aminophenyl group, which dyes are after being dried andpulverized in the shape of their alkali metal salts generally dark powders soluble in water; yielding upon reduction with zinc powder and acetic acid a dioxrpara'diamin, a '2.6 d iamino-5-naphthol-T-sulfom'c acid compound having in general the nucleus i and a diamino sub ituted derivative of 2.5.7-aminonaphthol sulfonic acid compound containing in the side chain an aminophenyl group: dyeing cotton shades which are rendered fast; to washing by an after treatment with formaldehyde, substantially as de scribed.

6. The herein described new disazo (ivostufi'having in a free state most probably the formula:

hich is after being driedand pnlvei-ized in the shape of its sodium selt a dark blue Dow- In testimony whereof I have hereunto set der soluble in water with a blue coloratmn: w my hand in the presence of two subscribing yielding upon reduction with.zinc powder witnesses. e end acetic acid dianisidin, 2.6-diamino-5- nephthol-isulfonic acid,meta-eminophenyl- MARTIN HERZBERG. [L 8.] naphthimidazole 5 oily-6 amino-7-su1fonic acid; and dyeing cotton blue shades which Witnesses: are rendered fast to washing by'en after Hxmm Nvm, treatment with formic aldehyde, substan- Ammrr Nmn. tielly as described.

copies of 111: patent my be obtained fur Ive cont! mh, by addressing the "Commissioner of intents.

' i Washington), a." r

It. is hereby certified that in Letters Patent No. 1,160,406, granted November 16, 1915, upon the application of Martin Herzberg, of Opladen, near Cologne, Germany, for an improvement in Azo Dye." an error appears in the printed specification requiring correction as follows: Page 2, line 125, formula, for the symbol CH,() read @11 0; and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Office.

Signed and sealed this 29th day of February, A. D., 1916.

[seen] R. F. WHITEHEAD,

Acting Gommissiomr of Patents. 

